The instant invention covers compounds having the generic structure: ##STR4## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein X represents the moieties: ##STR5## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents hydrogen or methyl with the provisos that (i) at least three of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen and (ii) when the dashed line is a carbon-carbon single bond and X is: ##STR6## then one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is methyl and the other represents hydrogen; wherein R.sub.5 represents hydrogen, MgX, MgR.sub.7, CdR.sub.7, ZnR.sub.7, Na, K or Li; wherein X represents Chloro, Bromo or Iodo; wherein R.sub.6 represents hydrogen or methyl; and wherein R.sub.7 represents lower alkyl; as well as uses of the above compounds, with the exception of the organometallic compounds of the genus, for augmenting or enhancing the aromas and/or taste of consumable materials.
Materials which can provide minty, camphoraceous, dry woody, sweet, fruity, woody patchouli, green, herbaceous, basil-like, citrus-like, bergamot-like, lime-like, grapefruit-like, peppery, precious-woody, vertiver-like, fresh, musky, lavender thyme, rosemary, sweaty, rooty and earthy aromas with floral, citrus, lavender and amber top-notes and backgrounds are known in the art of perfumery. Many of the natural materials which provide such fragrances and contribute desired nuances to perfumery compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the ususal variations of natural products.
By the same token, materials which can provide oriental, insence-like, peppery, blueberry-like, eucalyptol-like, minty, camphoraceous, floral, musk-like, rose-like, black pepper, spicey, patchouli, cooling, sandalwood-like, woody and walnut-like aromas with oriental, black pepper, peppery, minty, eucalyptol-like, camphoraceous, floral, rosey and patchouli-like tastes are well known in the art of flavoring for foodstuffs, toothpastes, chewing gums and medicinal products. Many of the natural materials which provide such flavor nuances and contribute desired nuances to flavor and compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Sweet, fruity, berry-like, cooling, woody and floral aroma and taste nuances are known in the art of the production of smoking tobaccos and smoking tobacco articles. Many of the natural materials which provide such aroma and taste nuances to smoking tobacco compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the essential flavor and/or fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of these synthetic materials either have the desired nuances only to a relatively small degree or else contribute undesirable or unwanted odor to the consumable compositions. The search for materials which can provide more refined patchouli-like aromas, for example, have been difficult and relatively costly in the areas of both natural products and synthetic products.
Artificial flavoring agents for foodstuffs have received increasing attention in recent years. For many years such food flavoring agents have been preferred over natural flavoring agents at least in part due to their diminished cost and their reproducible flavor qualities. For example, natural food flavoring agents such as extracts, concentrates and the like are often subject to wide variations due to changes in quality, type and treatment of the raw materials. Such variations can be reflected in the end products and result in unfavorable flavor characteristics in said end product. Additionally, the presence of the natural product in the ultimate food may be undesirable because of increased tendency to spoil. This is particularly troublesome in food and food uses where such products as dips, soups, chips, sausages, gravies and the like are apt to be stored prior to use.
The fundamental problem in creating artificial flavor agents is that the artificial flavor to be achieved be as natural as possible. This generally proves to be a difficult task since the mechanism for flavor development in many foods, medicinal products, chewing gums and toothpastes is not completely known. This is noticable in products having licorice, citrusy and vegetable flavor characteristics particularly.
Even more desirable are products that can serve to substitute for difficult-to-obtain natural perfumery oils and at the same time substitute for natural flavoring ingredients in foodstuffs, chewing gums, medicinal products, toothpastes, and smoking tobaccos.
Oxobicyclo compounds are known in the prior art. Thus, Nagakura, et al, Bull, Chem. Soc. Japan Vol. 48(10), 2995-6 (October 1975) discloses the compound defined according to the generic structure: ##STR7## produced by the reaction: ##STR8## wherein one of R.sub.1 ', R.sub.2 ', R.sub.3 ' or R.sub.4 ' is methyl and the others represent hydrogen. In addition, Conia and Rouessac, Bull. Soc. Chem. France 1953 (page 1925 et seq.) discloses processes for producing oxobicyclo compounds according to the following reaction steps: ##STR9##
The use of oxotricyclic derivatives in perfumery is disclosed in U.S. Pat. No. 3,996,169, issued on Dec. 7, 1976. Thus, in U.S. Pat. No. 3,996,169, a genus defined according to the structure: ##STR10## is disclosed, wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 is selected from the group consisting of hydrogen and methyl; and wherein the dashed line may be a carbon-carbon single bond or a carbon-carbon double bond. Members of this genus are indicated to be capable of altering, modifying, enhancing or emparting an aroma of or to consumable materials including colognes, perfumes and perfumed articles and such an aroma is of a patchouli type.
Arctander, "Perfume and Flavor Chemicals", 1969, Vol. 1 discloses the use in perfume compositions and foodstuff flavors of "decalinol", "decalone", "fenchone", and "fenchyl alcohol", thusly: